N-heteroacenes have been reported to exhibit efficient electron transport and thus to have potential applications in organic electronics. However, they are challenging to synthesize, and the current synthetic routes are inefficient. We have developed a two-step method towards the synthesis of N-heteroacenes. This method involves the synthesis of a precursor molecule that is converted to the desired N-heteroacene, of a given length, upon an acid-mediated cyclization of the precursor. We have shown that the route to the precursors via Buchwald-Hartwig Amination is synthetically efficient, and the acid-mediated cyclization to form the N-heteroacenes occurs in a 99% yield. Altogether, this two-step method results in higher yields than the classical methods (i.e. direct condensation of two molecules and oxidation of dihydro molecules) reported in the literature for the synthesis of N-heteroacenes. Studies of their optical and electronic properties with respect to the length of the N-heteroacene were carried out to confirm the prediction that the band gap decreases with increasing length. Both the synthetic route and characterization of the novel N-heteroacenes are important in optimizing the molecules for incorporation into devices.

Efficient synthesis of N-heteroacenes, 1D graphene analogues, for organic electronics

254th National Meeting (2017)

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